CN108553411A - Azelaic acid gelling agent and its preparation method and application - Google Patents
Azelaic acid gelling agent and its preparation method and application Download PDFInfo
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- CN108553411A CN108553411A CN201810825807.7A CN201810825807A CN108553411A CN 108553411 A CN108553411 A CN 108553411A CN 201810825807 A CN201810825807 A CN 201810825807A CN 108553411 A CN108553411 A CN 108553411A
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- azelaic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/194—Carboxylic acids, e.g. valproic acid having two or more carboxyl groups, e.g. succinic, maleic or phthalic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/60—Salicylic acid; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
Abstract
The present invention relates to azelaic acid gelling agents and its preparation method and application, belong to dermal drug technical field.The technical problem to be solved by the present invention is to provide a kind of azelaic acid gelling agent, which consists of the following components in percentage by weight:Azelaic acid 10~20%, salicylic acid 0.5~2%, 1~3%, 1,3 propylene glycol 60~74% of ZEN, remaining is water.The present invention uses specific raw material, azelaic acid is prepared into gelling agent, the transparent no precipitation of product, the preferable skin permeation of energy can be used in the treatment or prevention of acne, improve the cure rate of patients with acne.And component is simple, without be added preservative still can antibacterial, and preparation method is simple, of low cost.
Description
Technical field
The present invention relates to azelaic acid gelling agents and its preparation method and application, belong to dermal drug technical field.
Background technology
Acne is a kind of chronic inflammatory skin of pilosebaceous unit, teenager is mainly apt to occur in, to teenager
Psychology and social influence it is very big, but tended to after puberty nature mitigate or recovery from illness.Clinical manifestation is to be apt to occur in the powder of face
With the characteristics of the pleomorphism skin lesion such as thorn, papule, warts, tubercle.
It is shown according to skin disease association of China, the joint investigation of teenager federation of China:The incidence of China's acne is in year by year
Ascendant trend, 80% or more people it is different degrees of encountered acne problems.The severeer incidence of acne of the state of an illness accounts for young people's
1/3 or more.Wherein middle school student's patients with acne is 2.94 hundred million, and university student's patients with acne number is 1.33 hundred million, working in 25 years old or more
Race's white collar patients with acne more than 1.27 hundred million, three parts crowd amounts to people more than 5.5 hundred million.
According to incompletely statistics, China's anti-acne consumer just with annual 400-600 ten thousand person-times increase, the anti-acne market in China is just
Unprecedented rapidly rise undergoing.The anti-acne expense for the long acne person average annual 500 for having a mind to treatment with every is calculated, anti-acne city
The scale of field alreadys exceed 70,000,000,000.
Treatment for acne, the patients with acne of light moderate, which is typically chosen, does not treat and anti-acne on the market is voluntarily selected to produce
Product are treated, and the patients with acne of severe can arrive hospital and anti-acne mechanism is treated.Anti-acne mechanism on the market and production at present
Product can not thorough anti-acne, and have side effect.Hospital's anti-acne is not single-minded, beauty parlor's anti-acne is not professional, is weighed according to the Ministry of Public Health of China
Prestige counts, and in China, the complete cure rate of acne only has 32.95%.Therefore, it is badly in need of a kind of drug that can improve acne cure rate.
Azelaic acid also known as azalaic acid, appearance are white to yellowish monoclinic prism, acicular crystal or powder.With anti-
The effect of bacterium can directly inhibit and kill skin surface and intrafollicular bacterium;Reverse transcriptase generates the enzyme of dihydrotestosterone
It is excessive to reduce the skin oil and fat that dihydrotestosterone factor induces for process;The generation and effect of inhibitory activity oxygen radical, are conducive to resist
It is scorching.It is usually used in acne, acne rosacea, the treatment of pigmentation disorder etc..There is preferable permeability to skin, skin can be increased
Absorption function.But it is easily decomposed by high temperature, therefore, unsuitable high temperature is added when in use.It is polynary to be soluble in hot water, alcohol and part
Alcohol is slightly soluble in cold water, ether and benzene.
Currently, for azelaic acid product, paste making agent is often done, for example, application No. is 201610786026.2 patents of invention
A kind of acne paste and preparation method thereof is disclosed, is made of with paste morning paste and evening, evening therein includes second with paste
Raw material and emulsifiable paste matrix, the second raw material is by following material composition:10% azelaic acid, 0.1% Adapalene, 1% clindamycin,
1% salicylic acid, 1.5% oil azone and 0.2% Nepal's tortoise beetle ester.For another example, application No. is 201210230433.7 hairs
Bright patent discloses a kind of ointment for treating acne, by mass percentage by oxymatrine 3%, vitamin E 1%, azelaic acid
2%, menthol 0.5%, 2,901 5%, boric acid 3%, azone 2% is mixed and made into cream with 83.5% mass percent of emulsifiable paste matrix
Agent.
The above patent is that azelaic acid is done paste making agent, and the azelaic acid product in existing market also often does paste making agent, mesh
Be to increase its dissolubility and permeability.Azelaic acid is dissolved by the raw material of oiliness, while co-penetrant is added (generally
Oiliness raw material) promote its infiltration in skin, the cream or lotion that product can only be oil-containing are allowed in this way.Azelaic acid
Then oiliness raw material dosage is then more greatly for dosage, and the strong penetration-assisting agent amount of permeability is also bigger, and side effect is also bigger.Therefore, the nonyl of cream type
Diacid oil sense relatively is thick and heavy, and poor air permeability, side effect is larger, and substance content is not high.
Invention content
For disadvantages described above, the technical problem to be solved by the present invention is to provide a kind of novel form of azelaic acid, i.e. azelaic acid is solidifying
Jelly, for cream, which adds without oil components, prevents or the effect for the treatment of acne is good.
Azelaic acid gelling agent of the present invention, consists of the following components in percentage by weight:Azelaic acid 10~20%, salicylic acid
0.5~2%, ZEN 1~3%, 1,3-PD 60~74%, remaining is water.
Preferably, the azelaic acid gelling agent consists of the following components in percentage by weight:Azelaic acid 12~18%, bigcatkin willow
Acid 0.8~1.5%, ZEN 1.5~2.5%, 1,3-PD 65~72%, remaining is water..
Preferably, the azelaic acid gelling agent consists of the following components in percentage by weight:Azelaic acid 15%,
ZEN 2%, salicylic acid 1%, 1,3-PD 70%, water 12%.
Preferably, the water is deionized water.
Second technical problem that the present invention solves is to provide the preparation method of azelaic acid gelling agent of the present invention.
The preparation method of azelaic acid gelling agent of the present invention, includes the following steps:
A, it is uniformly mixed again with water after ZEN being dispersed in 1,3-PD, obtains solution A;
B, azelaic acid is dispersed in 1,3-PD, is heated to 65~80 DEG C, obtains solution B;
C, salicylic acid is dispersed in 1,3-PD, obtains solution C;
D, solution A, solution B and solution C are mixed, 55~65 DEG C stir and evenly mix, and then cool to room temperature, obtain azelaic acid
Gelling agent.
Wherein, step a, there is no time sequencing between step b and step c, can first carry out step a, can also first carry out
Step b can also first carry out step c, can also these three steps be carried out at the same time.It only need to be finally by solution A, solution B and molten
Liquid C mixing stirs evenly.
The present invention also provides azelaic acid gelling agent of the present invention answering in preparing prevention or Retinoids, Retin-A, Renova, Accutane
With.
The azelaic acid gelling agent of the present invention, can be used in the treatment or prevention of acne, improves the cure rate of patients with acne,
Patient is reduced since acne brings facial skin lesions, to mitigate the physiology and mental anguish that patient is brought due to acne.Together
When reduce patient's medical expense, reduce medical expenses.
Compared with prior art, the present invention has the advantages that:
The present invention uses specific raw material, azelaic acid is prepared into gelling agent, the transparent no precipitation of product can preferably permeate
Skin can be used in the treatment or prevention of acne, improve the cure rate of patients with acne.
The azelaic acid gelling agent of the present invention is the formula (opposite cream) of no oil addition.It, will not after Oily use
Increase the burden on skin and block pore, from the hidden danger without generating small pox;For long small pox skin, due to nonyl two
Stronger infiltration of acid itself, gelatinous azelaic acid is simpler than pasta infiltration to be easy, need not more many greases of sauce progress hydrotropy
It is oozed with helping, to avoid generating corresponding side effect because oily matter excessively introduces;In the anti-acne later stage, need follicular canal unimpeded
Be conducive to grease and the discharge of other metabolins, azelaic acid antiphlogistic and bactericidal, unimpeded follicular canal smoothly solves the problems, such as discharge, reduces
The recurrence of small pox may.
The azelaic acid gelling agent of the present invention, component is simple, without be added preservative still can antibacterial, and preparation method
Simply, of low cost.
Specific implementation mode
Azelaic acid gelling agent of the present invention, consists of the following components in percentage by weight:Azelaic acid 10~20%, salicylic acid
0.5~2%, ZEN 1~3%, 1,3-PD 60~74%, remaining is water.
Wherein, ZEN is polyacrylate cross-linked polymer -6, for the production of match BIC Corp of France, trade name SepiMAX
ZEN.Azelaic acid is electrolysed out electrolyte, can destroy the structure of carbomer, and ZEN is that a kind of having excellent resistance to electrolysis ability
Association polymer.The destruction that electrolyte is brought to formula can be resisted to the greatest extent, meanwhile, also have suspending stabilized well
Ability can produce with graceful sense of touch is moistened, assign the transparent aquagel product of swan velour texture.By the study found that only
Have and use ZEN, ability successful formulation obtains azelaic acid gelling agent.If ZEN additions are too low, obtained product is diluter, there is stream
Dynamic property, can not be prepared into gel, and if addition is excessive, the too dry influence of product uses.
Inventor is not the study found that azelaic acid influences the structure of ZEN, still, if only with water as solvent, production
Product transparency is too low, and after restoring room temperature, and azelaic acid crystal can be precipitated, and use absolute ethyl alcohol or 1,3-PD energy
Enough change the phenomenon that azelaic acid is precipitated, still, absolute ethyl alcohol can not change the transparency of product, and use 1,3-PD not only
It can solve the problems, such as that azelaic acid is precipitated, can also change the transparency of product, obtain the clear gel of alcohol-free taste.Therefore, this hair
Bright mixed using a certain amount of 1,3-PD and water is used as solvent, and obtained product is clear gel, and no crystal is precipitated, consistency
It is moderate, no mobility, alcohol-free taste.
Salicylic acid can make cutin softening fall off, and reduce pore obstruction, have preferably for puberty acne, acne vulgaris
Effect, root is it was found that the salicylic dosage of the present invention is preferably 0.5~2%.The salicylic acid of specific quantity is mixed with azelaic acid, tool
There is synergistic function, the therapeutic effect of acne can be improved.
Preferably, the azelaic acid gelling agent consists of the following components in percentage by weight:Azelaic acid 12~18%, bigcatkin willow
Acid 0.8~1.5%, ZEN 1.5~2.5%, 1,3-PD 65~72%, remaining is water.
Preferably, the azelaic acid gelling agent consists of the following components in percentage by weight:Azelaic acid 15%,
ZEN 2%, salicylic acid 1%, 1,3-PD 70%, water 12%.
Preferably, the water is deionized water.
Second technical problem that the present invention solves is to provide the preparation method of azelaic acid gelling agent of the present invention.
The preparation method of azelaic acid gelling agent of the present invention, includes the following steps:
A, it is uniformly mixed again with water after ZEN being dispersed in 1,3-PD, obtains solution A;
B, azelaic acid is dispersed in 1,3-PD, is heated to 65~80 DEG C, obtains solution B;
C, salicylic acid is dispersed in 1,3-PD, obtains solution C;
D, solution A, solution B and solution C are mixed, 55~65 DEG C stir and evenly mix, and then cool to room temperature, obtain azelaic acid
Gelling agent.
Wherein, step a, there is no time sequencing between step b and step c, can first carry out step a, can also first carry out
Step b can also first carry out step c, can also these three steps be carried out at the same time.It only need to be finally by solution A, solution B and molten
Liquid C mixing stirs evenly.
The present invention also provides azelaic acid gelling agent of the present invention answering in preparing prevention or Retinoids, Retin-A, Renova, Accutane
With.
The azelaic acid gelling agent of the present invention, can be used in the treatment or prevention of acne, improves the cure rate of patients with acne,
Patient is reduced since acne brings facial skin lesions, to mitigate the physiology and mental anguish that patient is brought due to acne.Together
When reduce patient's medical expense, reduce medical expenses.
The specific implementation mode of the present invention is further described with reference to embodiment, is not therefore limited the present invention
System is among the embodiment described range.It is raw materials used in embodiment to be:
ZEN:Bick is matched purchased from France;
Azelaic acid:Purchased from Shanghai Lin En developments in science and technology Co., Ltd;
Salicylic acid:Purchased from Shandong XinHua Pharmacy stock Co., Ltd;
1,3- propylene glycol:Corn source is purchased from DuPont Corporation;
Water:Self-produced deionized water.
Embodiment 1
Azelaic acid gelling agent is prepared as follows:
A, it is uniformly mixed again with water after ZEN being dispersed in 1,3-PD, obtains solution A;
B, azelaic acid is dispersed in 1,3-PD, is heated to 75 DEG C, stirring obtains solution B to transparent;
C, salicylic acid is dispersed in 1,3-PD, obtains solution C;
D, solution A, solution B and solution C are mixed, 60 DEG C stir and evenly mix, and then cool to room temperature, and obtain azelaic acid gel
Agent.
Wherein, the formula of each raw material is shown in Table 1.
Table 1
On the basis of the formula, it is artificially introduced a certain amount of bacterium (18000cfu/g or mould 8700cfu/g liquid), then
It takes the quantitative sample to measure its fungistatic effect, the results are shown in Table 2.
Table 2
Although from table 2 it can be seen that in system without be added preservative, still being capable of antibacterial.
Embodiment 2~4
Azelaic acid gelling agent is prepared according to method described in embodiment 1, wherein total dosage of each raw material is shown in Table 3.
Table 3
The anti-microbial property of the said goods is measured, it is found that the product of embodiment 2~4 also has anti-microbial property.
Comparative example 1
The practical formula experience for using for reference previous exploitation gel class product, by the matrix formulations composition design of azelaic acid gel
For:CP-940 (upper Haiyang jade for asking rain Industrial Co., Ltd.), azelaic acid (Shanghai Lin En developments in science and technology Co., Ltd), sodium hydroxide (divide
Analyse pure AR, Chengdu Ke Long chemical reagents factory), water (self-produced deionized water).
CP-940 is a kind of high molecular polymer, and aqueous solution is slowly swollen in water in acidity, the molecule meeting of curling
It is opened because of electric repulsion, to have the function that thickening, and sodium hydroxide and triethanolamine are then common neutralizers, it is contemplated that
The acidic nature of azelaic acid increases the ratio of CP-940 on the basis of doing gel-like formula in the past.We are by CP-940's
Based on 0.5%, 1.0%, 1.5%, 2.0% additive amount, 15% azelaic acid, result such as table 4 is added respectively in amount.
Table 4
As it can be seen that although azelaic acid is slightly soluble in cold water, but the structure of CP-940 is influenced very big.
In view of the electrolyte property of azelaic acid, we determine not having to alkali neutralization CP-940, configure base gel again, tie
Fruit is shown in Table 5.
Table 5
As it can be seen that no matter CP-940 neutralizes or do not neutralize, therefore the structure that azelaic acid can all destroy CP-940 uses CP-
940 matrix components for being used as gel are unworkable.
5 acne treatment of embodiment is tested
Using the product of Examples 1 to 4, while with azelaic acid cream, (formula of azelaic acid cream is:Azelaic acid 15%,
Salicylic acid 1%, emulsifiable paste matrix 84%) as a comparison case, acne treatment curative effect measurement is carried out, specific experimental method is:
The acne vulgaris patient of selection 14~40 years old, male or female, skin lesion are divided into 1~4 grade according to Pillsbury
Patient test.
Acne criteria for classification (improvement pillsbury stagings):0 grade:Very small acne or small papule (are not included in tested
Standard);I grade (slight):Being dispersed in property papule, acne have pimple, and disease damage is at 10~25;II grade (moderate):Mound in heaps
Rash, acne have pimple, and disease damage is at 25~50;III grade (severe):Papule, acne have pimple, disease damage number to be more than 50;
Tubercle is less than 5;IV grade (pole severe):Serious papule in heaps, acne, there is pimple, tubercle, tumour and scar.
Excluded cases standard:Local use crosses the drug person for the treatment of acne in 2 weeks;In 4 weeks system used antibiotic or
The drug person of other treatment acne;There are open wound or rotten to the corn face person in acne affected part;Because other diseases receiving has shadow to acne
Loud drug therapy person;The gestational period or women breast-feeding their children;The skin disease patient of observation curative effect, such as silver bits may be influenced with other
Disease, lupus erythematosus, steroid dependent dermatitis etc.;It is known to azelaic acid allergy sufferers.
Medication:Sooner or later it is coated in face acnes region with the medicine of a thin layer each 1 time, avoids being coated in eyes and membranous part
Position.Other externally applied drugs and antibiotic are not used during experiment.The course for the treatment of 6 weeks, every 2 weeks further consultation 1 time.
Observation index:Observation, record curative effect index and adverse reaction when further consultation in 2,4,6 weeks after first visit and treatment.Curative effect refers to
Mark includes inflammatory damage;Inflamed papules, warts;Non-inflammatory lesions:Hoary hair and blackhead.Observation index:Inflammatory damage counts:
Whelk, warts, tubercle and tumour are individually counted before treatment, counted respectively again in further consultation in the 2nd, the 4th and the 6th week;It is non-
Inflammatory damage counts:Facial hoary hair and blackhead are individually counted before treatment, distinguished again in further consultation in the 2nd, the 4th and the 6th week
It counts;
Laboratory examination:Blood, routine urinalysis are checked respectively for before and after treatment, wherein 12 are made liver function (TI, ALT), kidney function
It can (BUN, Cr) inspection.
Criterion of therapeutical effect:Main efficacy parameter is the reduction (summation of papule and warts) of total inflammatory damage number, at the 6th week
Carry out total effects evaluation.
Standard is as follows:
It cures:Damage reduces >=90%;
It is effective:Damage reduces 60%~89%;
It improves:Damage reduces 20%~59%;
In vain:The state of an illness is unchanged, or damage reduces result.
Each product selects 30 patients, observes its curative effect and adverse reaction, the results are shown in Table 6.
Table 6
Adverse reaction:Using the patient of product of the present invention, adverse reaction be mainly cusalgia, itch, erythema, oedema, drying,
Furfur, degree is relatively light, most of not deal with, does not influence to treat.
Claims (6)
1. azelaic acid gelling agent, it is characterised in that:It consists of the following components in percentage by weight:Azelaic acid 10~20%, bigcatkin willow
Acid 0.5~2%, ZEN 1~3%, 1,3-PD 60~74%, remaining is water.
2. azelaic acid gelling agent according to claim 1, it is characterised in that:It consists of the following components in percentage by weight:
Azelaic acid 12~18%, salicylic acid 0.8~1.5%, ZEN 1.5~2.5%, 1,3-PD 65~72%, remaining is water.
3. azelaic acid gelling agent according to claim 1, it is characterised in that:It consists of the following components in percentage by weight:
Azelaic acid 15%, ZEN 2%, salicylic acid 1%, 1,3-PD 70%, water 12%.
4. according to claims 1 to 3 any one of them azelaic acid gelling agent, it is characterised in that:The water is deionized water.
5. the preparation method of Claims 1 to 4 any one of them azelaic acid gelling agent, which is characterized in that include the following steps:
A, it is uniformly mixed again with water after ZEN being dispersed in 1,3-PD, obtains solution A;
B, azelaic acid is dispersed in 1,3-PD, is heated to 65~80 DEG C, obtains solution B;
C, salicylic acid is dispersed in 1,3-PD, obtains solution C;
D, solution A, solution B and solution C are mixed, 55~65 DEG C stir and evenly mix, and then cool to room temperature, and obtain azelaic acid gel
Agent.
6. application of the Claims 1 to 4 any one of them azelaic acid gelling agent in preparing prevention or Retinoids, Retin-A, Renova, Accutane.
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CN201810825807.7A CN108553411B (en) | 2018-07-25 | 2018-07-25 | Azelaic acid gel and preparation method and application thereof |
US16/960,025 US11026907B2 (en) | 2018-07-25 | 2019-06-26 | Azelaic acid gel, preparation method and application thereof |
PCT/CN2019/093004 WO2020019927A1 (en) | 2018-07-25 | 2019-06-26 | Azelaic acid gel, and preparation method and application thereof |
EP19840552.4A EP3708152B1 (en) | 2018-07-25 | 2019-06-26 | Azelaic acid gel, and preparation method and application thereof |
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WO2020019927A1 (en) * | 2018-07-25 | 2020-01-30 | 成都卓阳生物科技有限公司 | Azelaic acid gel, and preparation method and application thereof |
CN111249224A (en) * | 2020-03-19 | 2020-06-09 | 广州清淞泉生物科技有限公司 | Oil-free gel for treating acne and preparation method thereof |
CN111374938A (en) * | 2020-03-19 | 2020-07-07 | 广州清淞泉生物科技有限公司 | Oil-free gel containing azelaic acid and preparation method thereof |
CN111956637A (en) * | 2020-09-02 | 2020-11-20 | 谢志辉生物医药研究院(广州)有限公司 | Acne-removing ointment and preparation method thereof |
CN112220741A (en) * | 2020-11-18 | 2021-01-15 | 成都卓阳生物科技有限公司 | Azelaic acid gel and preparation method and application thereof |
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CN115154411A (en) * | 2022-07-15 | 2022-10-11 | 四川活颐化妆品有限公司 | Azelaic acid gel and its preparation method and use |
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WO2020019927A1 (en) * | 2018-07-25 | 2020-01-30 | 成都卓阳生物科技有限公司 | Azelaic acid gel, and preparation method and application thereof |
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CN111249224A (en) * | 2020-03-19 | 2020-06-09 | 广州清淞泉生物科技有限公司 | Oil-free gel for treating acne and preparation method thereof |
CN111374938A (en) * | 2020-03-19 | 2020-07-07 | 广州清淞泉生物科技有限公司 | Oil-free gel containing azelaic acid and preparation method thereof |
CN111374938B (en) * | 2020-03-19 | 2020-12-22 | 广州杨森药业有限公司 | Oil-free gel containing azelaic acid and preparation method thereof |
CN111956637A (en) * | 2020-09-02 | 2020-11-20 | 谢志辉生物医药研究院(广州)有限公司 | Acne-removing ointment and preparation method thereof |
CN112220741A (en) * | 2020-11-18 | 2021-01-15 | 成都卓阳生物科技有限公司 | Azelaic acid gel and preparation method and application thereof |
WO2022105225A1 (en) * | 2020-11-18 | 2022-05-27 | 成都卓阳生物科技有限公司 | Azelaic acid gel, preparation method therefor and application thereof |
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WO2020019927A1 (en) | 2020-01-30 |
EP3708152A1 (en) | 2020-09-16 |
US20200345672A1 (en) | 2020-11-05 |
US11026907B2 (en) | 2021-06-08 |
EP3708152A4 (en) | 2021-03-03 |
EP3708152B1 (en) | 2022-06-01 |
CN108553411B (en) | 2020-05-12 |
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